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Puerto Rico Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in October 2026 or 2027, we have 19 unique cruise itineraries and 106 departures available, operated by seven of the world's leading cruise lines departing in October.
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19 Cruises (106 Cruise Departures)
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (5)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$725
Oceanview
$775
Balcony
$974
Suite
$1,200
From
US$725
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$1,018
Oceanview
$1,218
Balcony
$1,418
Suite
$2,754
From
US$1,018
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,325
Oceanview
$1,512
Balcony
$1,527
Suite
$2,652
From
US$1,325
Save 811
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$777
Oceanview
$938
Balcony
$1,170
Suite
$2,015
From
US$777
Save 463
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Black Friday Sale
Inside
$556
Oceanview
$646
Balcony
$787
Suite
$1,061
From
US$556
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise
 (5)

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 23 October 2026
Visit: Spain, Portugal, Sint Maarten, Puerto Rico
Viking $999 Air Deal
Inside
-
Oceanview
-
Balcony
$3,599
Suite
$5,999
From
US$3,599
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,320
Oceanview
$1,391
Balcony
$1,534
Suite
$3,058
From
US$1,320
Save 962
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Nov 2025 to Oct 2027
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$394
Oceanview
$504
Balcony
$714
Suite
$1,424
From
US$394
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$1,080
Oceanview
$1,290
Balcony
$1,490
Suite
$5,415
From
US$1,080
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Black Friday Sale
Inside
$614
Oceanview
-
Balcony
$804
Suite
$1,233
From
US$614
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Bonus Onboard Credit
Exclusive Savings
Inside
$581
Oceanview
$653
Balcony
$1,369
Suite
$1,583
From
US$581
Save 373
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$1,357
Oceanview
$1,537
Balcony
$1,797
Suite
$6,425
From
US$1,357
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$904
Oceanview
$954
Balcony
$1,129
Suite
$3,052
From
US$904
Save 466
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,509
Oceanview
$1,769
Balcony
$2,304
Suite
$4,011
From
US$1,509
Per Person
View Trip
8 Day Valiant's Haunted Halloween Soiree with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Black Friday Deal
Inside
-
Oceanview
$1,183
Balcony
$1,393
Suite
$4,130
From
US$1,183
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$1,160
Oceanview
$1,380
Balcony
$1,610
Suite
$5,747
From
US$1,160
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Black Friday Sale
Inside
$1,143
Oceanview
$1,378
Balcony
$1,718
Suite
$2,324
From
US$1,143
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Princess Plus
Inside
$925
Oceanview
$1,125
Balcony
$1,475
Suite
$1,650
From
US$925
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$1,214
Oceanview
$1,444
Balcony
$1,674
Suite
$6,099
From
US$1,214
Per Person
View Trip
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